Dobie and Hummel (2001) asserted that the school superintendency is the most male-dominated position within the field of education. According to a 1992 study, 72% of educators were women; however, only 13.2% of superintendents are women (Glass, 1992). The most recent survey by the American Association of School Administrators (AASA) found that progress had been made, as 24.1% of the school district CEOs were female (Kowalski, McCord, Petersen, Young, & Ellerson, 2010); however, these data continue to reflect a disparity. Statistics indicate that the female superintendent operates in a world not of her making and in a paradigm designed around men. Considering that 50% of students in the classroom and 72% of teachers are female, nowhere does one see a dissonance that is greater than in the area of the school superintendency. Yet, the data tell only part of the story. The image the data conjure up is of a passive victim, yet women are increasingly making significant contributions in terms of defining district leadership. This review of the literature is based on a three-part conceptual framework suggesting that women lead in different ways than men do based on physiological and socialization differences, which are viewed negatively by the male-dominated culture. This gender bias is expressed in both the glass ceiling women face when approaching the superintendency as well as their experiences as superintendents. (Contains 4 footnotes.)